PT92617B - PROCESS FOR THE PREPARATION OF SUBSTITUTED DERIVATIVES OF DIONAS AND HERBICIDAL COMPOSITIONS CONTAINING THEM - Google Patents

Abstract

A herbicide exhibiting high herbicidal activity against a variety of weeds and being highly safe for useful crops can be obtained through the use of a heterocyclic compound represented by the following general formula (I): wherein R represents a group represented by the following formula: X represents an oxygen atom or a sulfur atom; R¹ represents a halogen atom or a lower alkyl group; R² represents a hydrogen atom or a methyl group; R³ represents a halogen atom, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a lower alkylthio group, a cyano group or -COOR⁴ (R⁴ is a lower alkyl group, a lower alkoxyalkyl group or a tetrahydrofurfuryl group); m is 0, 1 or 2 and n is 0, 1, 2 or 3.

Description

DESCRIPTION

GIVES

INVENTION PATENT

No • 92 617

APPLICANT: AGRO-KANESHO CO., LTD., Japanese, industrial, based in 4-1.Marunouchi 2-chome.Chiyoda-ku, Tokyo, Japan.

EPIGRAPH: · 'SUBS DERIVATIVE PREPARATION PROCESS

TITLE OF DIONAS AND HERBICID COMPOSITIONS THAT CONTAIN THEM

INVENTORS: Nobuo Onodera, Shinzo Someya, Seigo Koura and

Shigenori Sagami.

Claim of the right of priority under Article 4 of the Paris Convention of 20 March 1883.

Japan with no. 50245/1989 on March 2, 1989.

INP1 MOO U3 RF 15732

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PATENT N2. 92 617

X,

Process of preparing substituted derivatives of diones and herbicidal compositions containing them so that

AGRO-KANESHO CO., LTD., Intends to obtain privilege of invention in Portugal.

RESUME

The present invention relates to the process of preparing a heterocyclic compound represented by the following general formula:

c t in which R represents a group represented by the following formulas:

R ¹ ),

-CH,

R ³ ) or (hi position or position (3)

X represents an oxygen atom or a sulfur atom; RÍ represents a halogen atom or a lower alkyl group; R ² represents a hydrogen atom or a methyl group; R4 represents a halogen atom, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a lower alkylthio group

4 - or, a cyano or -COOR group (R and a lower alkyl group, a lower alkoxyalkyl group or a tetrahydrofurfuryl group); m is 0, 1 or 2ené0, 1, 2 or 3 which comprises the step of reacting a compound represented by the following formula:

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with a compound represented by the following general formula:

in which R has the same meanings as those previously defined - and Y represents a halogen atom or -O-SO „-R (in which R represents an alkyl group or an aryl group).

The invention also relates to the process of preparing herbicidal compositions which exhibit potent herbicidal activity against various weeds and are very safe in useful crops

ΊΟ 370

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-3 DESCRIPTIVE MEMORY

BACKGROUND OF THE INVENTION (Field of the Invention)

The present invention relates to a process for preparing new heterocyclic compounds, and the process for preparing a herbicidal composition containing said compounds as effective components.

(Reference to prior art)

In the cultivation of fields and gardens, intensive weed control work has been carried out using a variety of herbicides. However, harvests are harmed by these herbicides and herbicides remain in the environment and cause environmental pollution. In this way, it has been desired to develop a chemical product for agricultural use that shows constant high efficiency even when used in a small amount, and that can be used safely.

There are a large number of patents relating to herbicides containing heterocyclic compounds, particularly compounds of the imide type, as effective components and in which a variety of compounds are described. Among the many compounds described in known patents, those that relate relatively more closely to the present invention are, for example, the following:

(Japanese Unexamined Patent Application No. 139359/1980);

370 u ..... '

- £ ,,

File: OP 89257 - 4 - (Japanese Unexamined Patent Application No. 209290/1982);

(Unexamined Japanese Patent Application No. 99488/1983);

(Japanese Unexamined Patent Application NS. 219167/1983); and

ch ₃ (GB 2150929A)

However, these compounds suffer from several problems. For example, they have only insufficient herbicidal activity and cause damage to crops. As such, none of the compounds has yet been launched on the market.

OBJECTIVE AND SUBJECT OF THE INVENTION

One of the objectives of the present invention is to provide a new compound that shows a high herbicidal activity and a great safety in relation to the cultivated species.

Another object of the present invention is the process of preparing the new compound mentioned above.

Another object of the present invention is a new herbicidal composition containing a new compound mentioned above as with

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-5X ·· ('effective component.

To develop a useful herbicide that makes it possible to overcome the problems mentioned, the inventors of this invention have carried out several studies, particularly on heterocyclic compounds and found that the compounds represented by the following general formula (I) (hereinafter referred to as present compounds) invention) show high herbicidal activity and can be used safely for a variety of cultivated species. They therefore constitute the aim of the present invention.

More specifically, in this way, the present invention relates to the process of preparing a new heterocyclic compound represented by the following general formula (I):

where R represents a group represented by the following formula:

or

m n

(oi position or 0 position);

X represents an oxygen atom or a sulfur atom; R represents a halogen atom or a lower alkyl group; R4 represents a hydrogen atom or a methyl group; R ^J represents a

-670 370

File: OP 89257 halogen atom, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a lower alkylthio group, a cyano or -COOR group (R and a lower alkyl group, a lower alkoxyalkyl group or a tetrahydrofurfuryl group); m is 0, 1 or 2ené0, 1, 2 or 3.

In this way, the present invention refers to the process of preparing a heterocyclic compound represented by the general formula

II O-R

O where R represents a group represented by the following formula:

or

(tx position or β position);

X represents an oxygen atom or a sulfur atom; R ¹ represents a halogen atom or a lower alkyl group; R repre

- - 3 ^- contains a hydrogen atom or a methyl group; R represents a halogen atom, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a lower alkylthio group. 4, or, a cyano or -COOR group (R and a lower alkyl group, a lower alkoxyalkyl group or a tetrahydrofurfuryl group); m is 0, 1 or 2 and n is 0, 1, 2 or 3 which comprises the reaction step of a compound represented by the following formula:

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with a compound represented by the following general formula:

R - Y where R has the previously defined meaning and Y represents

- - 5 5 is a halogen atom or -O-SC4 R (where R represents an alkyl group or an aryl group).

In accordance with another aspect thereof, the present invention relates to the process of preparing a herbicidal composition containing a heterocyclic compound represented by the following general formula (I) as an effective component:

where R represents a group with the following formula:

or

(hi position or position (3)

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-8. 1 X represents an oxygen atom or a sulfur atom; R represents a halogen atom or a lower alkyl group; R ^- repre ~

it contains a hydrogen atom or a methyl group; R represents a halogen atom, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a lower alkylthio group

4 - ’~ or, a cyano or -COOR group (R and a lower alkyl group, a lower alkoxyalkyl group or a tetrahydrofurfuryl group); m is 0, 1 or 2 and n is 0, 1, 2 or 3.

DETAILED EXPLANATION OF THE INVENTION

The compounds of the present invention are new compounds that were first synthesized by the inventors of the present invention.

The herbicides of the present invention, which comprise the compound of the present invention as an effective component, show, as will be explained in the examples which follow, excellent herbicidal activity against various weeds which constitute a problem in the treatment of water in flooded fields. These herbs include those that belong to the group of herbs such as Echinichloa crusgalli, such as broadleaf herbs such as the bastard pimpinela rotala flowers on the cob, gen. callistriche and ducktongue weed, and herbs belonging to the ciperaceae family such as the smallflower umbrellaplant, slender spikrush and water nutgrass. They exhibit particularly good activity against upland broadleaf herbs. Examples of these herbs are the mustard plant, the mast of America, the apparinas, the gallium sp., The chickweed, the kenopods, the nettle, vulgar potted, green amaranth, thistle, Echinochloa crusgalli, sanguinar and mauve. In addition, grass species such as corn, rice and wheat are not damaged by the herbicides of the present invention and herbicides show high safety.

Typical examples of the compounds of the present invention represented by the general formula (I):

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O include the following: compounds having R, 2-tenyl, 5-chloro-2-tenyl, 2-phenoxyethyl, 2- (2-methylphenoxy) ethyl, 2— (3-merylphenoxy) ethyl, 2- (4- methylphenoxy) ethyl, (2-chlorophenoxy) ethyl,

2- (3-chlorophenoxy) ethyl, 2- (4-chlorophenoxy) ethyl, 2- (4-fluorophenoxy) ethyl, 2- (4-cyanophenoxy) ethyl, 2- (4-ethoxycarbonylphenoxy) ethyl, 2- (3- trifluoromethylphenoxy) ethyl, 2- (4-ethoxyphenoxy) ethyl, 2- (4-methyl thiophenoxy) ethyl, 2- (2,4-dimethylphenoxy) ethyl, 2- (3,4-dimethylphenoxy) ethyl, 2- (3, 5-dimethylphenoxy) ethyl, 2- (2,4-dichlorophenoxy) ethyl, 2- (3,4-dichlorophenoxy) ethyl, 2- (2-methyl-4-chlorophenoxy) ethyl, 2- (2,3,

5-trimethylphenoxy) ethyl, 2- (2,3,6-trimethylphenoxy) ethyl, 2- (3,5-dimethyl-4-chlorophenoxy) ethyl, 2-phenylthioethyl, 2- (4-methylphenylthio) ethyl 2- ( 4-chlorophenylthio) ethyl, 2- (1-naphthoxy) -ethyl, 2- (2-naphthoxy) ethyl, 2-phenoxy-1-methylethyl, 2- (4-methylphenoxy) -1-methylethyl, 2- (4- chlorophenoxy) -1-methylethyl, 2- (4-isopropylphenoxy) -1-methylethyl, 2- (4-ethoxyphenoxy) -1-methylethyl, 2- (4-methylthiophenoxy) -1-methylethyl, 2- (4-ci anophenoxy) -1-methylethyl, 2- (3,5-dimethylphenoxy) -1-methylethyl, 2- (2,

4-dichlorophenoxy) -1-methylethyl, 2- (4-methylphenylthio) -1-methylethyl and 2- (2-naphthoxy) -1-methylethyl.

The compounds of the present invention can be prepared by a process represented by the following reaction sequence:

O

(II) (UI) (I)

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-1 0In these formulas, R and Y have the meanings defined previously.

The compounds of the present invention represented by the general formula (I) can be obtained by reacting a compound represented by the formula (II) with a compound represented by the general formula (III), at a temperature between room temperature and the boiling point of a used solvent, in the presence of an excess of a base.

The Y substituent of compound R - Y is preferably a chlorine atom, a bromine atom, -O-SO ₂ CH ₂ or

Examples of solvents include the usual inert solvents, for example, ketones such as acetone; ethers such as tetrahydrofuran, dioxane and dimethoxyethane; esters such as ethyl acetate, aromatic hydrocarbons such as benzene and chlorobenzene; polar solvents such as dimethylformamide and N-methylpyrrolidone. These solvents can be used alone or in combination.

Examples of basic materials include inorganic bases such as potassium carbonate, sodium carbonate, potassium hydroxide, sodium hydroxide, sodium alcoholates, sodium hydride; and organic amines such as triethylamine and DBU. They are preferably used in excess and are generally between 1.1 and 5.0 times the amount of reagents (expressed in molar amount).

The reaction temperature can be fixed at any value as long as it is between room temperature and the boiling point of the solvent used. Preferably, the temperature is between 30 and 150 ° C, and particularly between 40 and 100 ° C.

The reaction time can vary depending on the other conditions established, but generally, the reaction can be finished in 1 to 10 hours.

The reaction products can be separated from the resulting reaction mixture in a usual manner and can be optionally and fa70 370

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-11 easily purified by recrystallization or by a column chromatography technique.

according to the following reaction scheme:

The herbicidal composition of the present invention can be formulated in the form of an emulsifiable concentrate, an oily solution, a hygroscopic powder and granules, by a standard preparation process using the aforementioned compounds and auxiliary agents for chemicals for agricultural use normally used in this area.

These various formulations can practically be used as such or after dilution with water to a desired concentration.

Examples of auxiliary agents for chemicals for agricultural use are diluents, surfactants, stabilizers, adhesion agents, aerosol propellants, synergistic agents, solid carriers, effect retarders, and dispersion-stabilizing agents. Specific examples of diluents include water, hydrocarbons, alcohols, ethers, alcoholic ethers, ketones, esters, starches, and sulfoxides. Specific examples of solid vehicles include inorganic particles and powders, such as calcium oxide, magnesium oxide, gypsum, calcium carbonate, silica soil, perlite, pumice, diatomaceous earth, alumina, zeolites, mineral clay (eg talc, vermiculite and kaolinite); plant dust and particles such as starch, grains and dextrose; and synthetic resin powder

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-1 2 such as phenolic resins, carbon resins and vinyl chloride resins. Specific examples of surfactants include anionic surfactants such as alkyl sulfuric acid esters, aryl sulfonic acids, succinic acid salts and polyethylene glycol alkyl alkyl ethers; cationic surfactants such as alkylamines and polyoxyethylene alkylamines; non-anionic surfactants such as polyoxyethylene glycol ethers, polyoxyethylene glycol esters and polyhydric alcohol esters and amphoteric surfactants.

Examples of specific preparations include the following:

Preparation Example 1 (Emulsifiable Concentrate)

20 parts by weight of an effective component, 60 parts by weight of xylene and 20 parts by weight of Sorpol 2806B (brand of a surfactant available from TOHO CHEMICAL INDUSTRI ES CO., LTD.) Are mixed with stirring to obtain an emulsifiable concentrate

Preparation Example 2 (Hygroscopic powder)

10 parts by weight of an effective component are crushed and mixed together, 87 parts by weight of Zieclite, 1.5 parts by weight of Neoplex powder (brand available from KAO CORPORATION) and 1.5 parts by weight of Sorpol 800A (brand of a surfactant available from TOHO CHEMICAL INDUSTRIES CO., LTD.), To form a hygroscopic powder.

The herbicides of the present invention can be used in a similar way to conventional herbicides. For example, they can be used to treat the soil before the germination of weeds from mountainous terrains or in the initial phase of their germination. Alternatively, for wetland weeds, the herbicides of the present invention can be used to treat the soil after planting and rooting, for example, rice and before or immediately after weed germination.

The dose of herbicides of the present invention can be appropriately selected depending on several factors such as the method of application, the objectives, the age and the state of development of the herbs, but is generally between 0.01 to 10 kg, preferably , 0.05 to 5 kg per hectare, expressed in quantity of

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-1 3 effective component.

The present invention will be explained in more detail below with reference to the following Examples, but the present invention is not limited by these specific Examples.

Example 1; Preparation of 2- [4-chloro-2-fluoro-5- (5-chloro-2-phenyloxy) phenii] -5,6,7,8-tetrahydroimidazo- [1,5a] -pyridine-1,3 (2H,

8aH) -dione (compound NS. 1).

0.83 g of 2- (4-chloro-2-fluoro-5-hydroxyphenyl) -5 was stirred,

6,7,8-tetrahydroimidazo- [1,5a] -pyridine-1,3 (2H, 8aH) -dione together with 1.40 g of potassium carbonate, 10 ml of dimethoxy ethane and 0.42 g of 5-chloro-2-phenyl chloride at a temperature of 60 to 65 ° C for 5 hours. After cooling the reaction mixture, water was added to precipitate the crystals, followed by filtration of the crystals and washing with water, thereby obtaining crude crystals. The crystals were purified with ether to obtain 0.70 g of the title compound.

= 135 ~ 137 ° C

Example 2: Preparation of 2- {4-chloro-2-fluoro-5- (2-phenoxyethoxy) phenii) -5,6,7,8-tetrahydroimidazo- [1,5a] -pyridine-1,3 ( 2H, 8aH) -dione (compound Ns. 2).

0.80 g of 2- (4-chloro-2-fluoro-5-hydroxyphenyl) -5,6,7,8-tetrahydroimidazo- [1,5a] -pyridine-1,3 ( 2H, 8aH) -dione together with 1.50 g of potassium carbonate, 10 ml of acetone and 0.65 mg of 2-phenoxyethyl bromide for 8 hours. After allowing the reaction mixture to cool, water was added to precipitate the crystals, followed by filtering the crystals and washing them with water, obtaining crude crystals. The crystals were then purified with n-hexane to obtain 0.64 g of the title compound.

Mp = 133 135 ° C

Example 3: Preparation of 2- [4-chloro-2-fluoro-5- {2- (4-cyanophene xi) ethoxy) phenii] -5,6,7,8-tetrahydroimidazo- [1,5a] - pyridine-1,3 (2H,

8aH) -dione (compound No. 7).

0.80 g of 2- (4-chloro-2-fluoro-5-hydroxyphenyl) -5.6,

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-1 47,8-tetrahydroimidazo- [1,5a] -pyridine-1,3 (2H 8aH) -dione together with 1.50 g of potassium carbonate, 10 ml of dimethylformamide and 0.72 g of tosylate 2- (4-cyanophenox $ etib at a temperature of 70 to 75 ° C for 6 hours. After allowing the reaction mixture to cool, water was added, followed by extraction of the mixture with benzene, washing with water, drying over sulfate of anhydrous magnesium and concentration of the extract under reduced pressure The resulting residue was purified by silica gel column chromatography to obtain 0.54 g of the title compound.

= 156.5 ~ 157.5 ° C

Example 4: Preparation of 2- [4-chloro-2-fluoro-5- | 2- (3,4-dimethyl phenoxy) ethoxy] -phenyl] -5,6,7,8-tetrahydroimidazo- [1, 5a] -pyridine-1,3 (2H, 8aH) -dione (Compound No. 11).

0.75 g of 2- (4-chloro-2-fluoro-5-hydroxyphenyl) -5,6,7,8-tetrahydroimidazo- [1,5a] -pyridine-1,3 (0.75 g) were heated to reflux 2H, 8aH) -dione together with 1.39 g of potassium carbonate, 15 ml of dimethoxyethane and 0.69 g of 2- (3,4-dimethylphenoxy) ethyl bromide for 5 hours. After allowing the reaction mixture to cool, water was added followed by extraction of the mixture with benzene, washing with water, drying over anhydrous magnesium sulfate and concentration of the extract under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 0.54 g of the title compound.

= 100 - 103 ° C.

Example 5: Preparation of 2- [4-chloro-2-fluoro-5- {2- (4-chlorophenoxy) -1-methylethoxy | phenyl] -5,6,7,8-tetrahydroimidazo- [1,5a] -pyridine-1,3 (2H, 8aH) -dione (Compound No. 15).

0.75 g of 2- (4-chloro-2-fluoro-5-hydroxyphenyl) -5,6,7,8-tetrahydroimidazo- [1,5a] -pyridine-1,3 (0.75 g) were heated to reflux 2H, 8aH) -dione together with 1.39 g of potassium carbonate, 15 ml of dimethoxyethane and 0.72 g of 2- (4-chlorophenoxy) -1-methylethyl tosylate for 4 hours. After allowing the reaction mixture to cool, water was added, followed by extraction of the mixture with benzene, washing with water, drying over anhydrous magnesium sulfate and concentration of the extract under reduced pressure. The resulting residue was

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-15 purified by silica gel column chromatography to obtain 0.69 g of the title compound.

= 123.5 ~ 125 ° C

Typical examples of compounds of the present invention prepared according to procedures similar to those of the previous Examples (including those prepared in the previous Examples) include those indicated in Table I below.

Table I: Typical Examples of the Compounds of the Invention:

Comp. Ν2, 1

135 to 137

Cc) ^CH 2C1

133 to 135

104 to 106

-CH ₂ C » ₂ O -

CH ·

119 to 121

CH

- ^c H2 ^c »2 ° - ^ Q ^

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-16r

Pr ......

138.5 to 140

-ch ₂ ch ₂ o

-CH ₂ CK ₂ O

-ch ₂ ck ₂ o

-ck ₂ ch ₂ o

Cl

CN

144.8 to 146.4

156.5 to 157.5

157 to 159

resinous form IV (cm ^-1 ):

C = O: 1782, 1728

3H: 795

162.5 to 164

-ch ₂ ck ₂ o

...

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100 to 103

CH ₇ I 4

-chch ₂ o

resinous form IV (cm “ ¹ ):

C = O: 1782, 1728

2H: 819 resinous form IV (cm “ ¹ ):

C = O: 1782, 1725

5H: 756 resinous form IV (cm ^_1 ):

C = O: 1782, 1728

2H: 828

123.5 to 125

to 101

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-1817

CHn

I

-CHCH ₂ O

CHo I ^J

-chch ₂ o

^OC 2 ^H 5 ^CH 3

-chch ₂ o sch ₃

88.5 to 91 resinous form

IV (cm):

0 = 0: 1782, 1728

2H: 819

131.5 to 134

136.5 to 139

Example 6: Soil Treatment Test for Rice Plantation.

In 1/5000 Ares by Wagner Pots, soil was placed in a flooded land, sowing the flooded land with herb seeds indicated in Table II. After compacting the bed, the rice sprouts in their 2-leaf phase (species Sasanishiki sp.) Were transplanted and kept under flood conditions of about 4.0 cm of water. The herbicides of the present invention, prepared according to Preparation Example 1, were diluted with a desired amount of water and were evenly sprayed on the water surface in the amounts indicated in Table II at the early development stages of Echinochloa Crusgalli broadleaf herbs or the like. As a control, N- (4-chloro-2-fluoro-5-isopropoxyphenyl) -3.4 was used,

5,6-tetrahydrophthalimide as described in Patent Application Ja70 370

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-19 Unexamined woman NS. 163365/1982. Growing conditions for weeds and crops were observed 20 days after treatment with agricultural chemicals and the results summarized in Table II were obtained. In Table II, the herbicidal effectiveness was estimated according to the following 6-point scale. Furthermore, crop damage caused by chemicals for agricultural use

glue used were also estimated according to the same scale. 0. . . . 1 . . . . 2 . . . . 3 4. . . . 5. . . . control speed 0 to 9% 29% 49% 69% 89% 100% II II II II II  10 to  30 to  50 to  70 to  90 to Table II Comp . Dose Plant in Echinochloa Smallflow ” duckton Herbs NQ. (g / a) rice crusgalli er umbrel gue weed home sheet laplant annual ga 1 10 0 5 5 5 5 1 2/5 0 5 5 5 4 1 0.625 0 5 5 5 4 2 10 0 5 5 5 5 2 2.5 0 5 5 5 5 2 0.625 0 5 5 5 5 3 10 0 5 5 5 5 3 2.5 0 5 5 5 5 3 0.625 0 5 5 5 5 4 10 0 5 5 5 5 4 2/5 0 5 5 5 5 4 0.625 0 5 5 5 5 5 10 0 5 5 5 5 5 2.5 0 5 5 5 5 5 0.625 0 5 5 5 5 6 10 1 5 5 5 5 6 2.5 0 5 5 5 5 6 0.625 0 5 5 5 5

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File: OP 89257 -20- 7 10 0 5 5 5 5 7 2.5 0 5 5 5 4 7 0.625 0 4 5 4 3 8 10 0 5 5 5 5 8 2.5 0 5 5 5 5 8 0.625 0 4 5 5 5 9 10 0 5 5 5 5 9 2.5 0 5 5 5 5 9 0.625 0 5 5 5 5 10 10 0 5 5 5 5 10 2.5 0 5 5 5 5 10 0.625 0 5 5 5 5 1 1 10 0 5 5 5 5 11 2.5 0 5 5 5 5 1 1 0.625 0 5 5 5 5 12 10 0 5 5 5 5 12 2.5 0 5 5 5 5 12 0.625 0 5 5 5 5 13 10 0 5 5 5 5 13 2.5 0 5 5 5 5 13 0.625 0 5 5 5 5 14 10 0 5 5 5 5 14 2.5 0 5 5 5 5 14 0.625 0 4 5 5 5 15 10 0 5 5 5 5 15 2.5 0 5 5 5 5 15 0.625 0 5 5 5 5 16 1 0 0 5 5 5 5 16 2.5 0 5 5 5 5 16 0.625 0 5 5 5 5 1 7 10 0 5 5 5 5 1 7 2.5 0 5 5 4 5 1 7 0.625 0 5 5 3 5 18 10 0 5 5 5 5 18 2.5 0 5 5 5 5 18 0.625 0 5 5 5 4 1 9 10 0 5 5 5 5

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19 2.5 0 19 0.625 0 20 10 0 20 2.5 0 20 0.625 0 Comp. 10 2 Ex. 2.5 2 0.625 1

5 5 4 3

5 5 5

3

Comparison Compound: N- (4-chloro-2-fluoro-5-isopropoxyphenyl) -3,4,5,6-tetrahydrophthalimide.

Example 7: Foliage Treatment

Mountainous soil was placed in plastic pots measuring 22 cm x 16 cm, after which the soil was sown with wheat, corn and soybean seeds in a defined amount and the seeds were covered with soil containing weed seeds such as mallow, green amaranth and thistle in a thickness of about 1 cm. The following compounds were sprayed in an amount indicated in Table III when plants such as wheat reached the stage of 2 to 2.5 leaves. The growth conditions of plants and herbs were observed 14 days after spraying the compounds and the results shown in Table III were observed.

As a control compound, the same compound as used in Example 6 was used and the herbicidal efficacy of each compound and the damage to crops caused by the compounds were also evaluated in the same way as in Example 6.

Table III

Comp. Dose Soy Wheat Corn Amaranth Malva Thistle N2. (g / 1 Ga) green 1 20 1 0 0 5 5 5 1 10 0 0 0 5 5 5 2 20 1 0 0 5 5 5 9 10 0 Ç 0 5 5 4 3 20 1 0 0 5 5 5 3 10 0 0 0 5 5 5

File: OP 89257 '

d. '

4 20 0 0 0 5 5 4 4 10 0 0 0 5 5 3 5 20 0 0 0 5 5 5 5 10 0 0 0 5 5 4 6 20 0 0 0 5 5 4 6 10 0 0 0 5 5 3 7 20 0 0 0 5 5 5 7 10 0 0 0 5 5 4 8 20 0 0 0 5 5 4 8 10 0 0 0 5 5 3 9 20 1 0 0 5 5 5 9 10 0 0 0 5 5 5 10 20 Q 0 0 5 5 5 10 10 0 0 0 5 5 4 11 20 0 0 0 5 5 5 11 10 0 0 0 5 5 5 12 20 0 0 0 5 5 5 12 10 0 0 0 5 5 5 13 20 1 0 0 5 5 5 13 10 0 0 0 5 5 5 14 20 0 0 0 5 5 5 14 10 0 0 0 5 5 5 15 20 0 0 0 4 5 4 15 10 0 0 0 2 4 3 16 20 0 0 0 5 5 5 16 10 0 0 0 5 5 4 1 7 20 0 0 0 5 5 5 17 10 0 0 0 4 4 4 18 20 1 0 0 5 5 5 18 10 0 0 0 5 5 5 19 20 0 0 0 5 5 5 19 1 0 0 0 0 4 5 4 20 20 0 0 0 5 5 5 20 10 0 0 0 4 5 4 Comp. 20 4 2 2 5 5 4 Ex. 10 3 1 1 3 4 3

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According to the present invention, new compounds with excellent herbicidal activity and with high safety can be obtained as herbicides and processes for preparing such compounds. In addition, the herbicides of the present invention containing these compounds as effective components exhibit high herbicidal activity which makes it possible to consistently eradicate various weeds. Furthermore, they are highly safe for various useful plants and, as such, can be used in flooded fields and / or mountain fields without causing damage, in particular in upland rice or wheat and maize crops.

Claims (12)

1 - Process of preparation of a heterocyclic compound represented by the following general formula: The one in which R represents a group represented by the following formulas: X represents an oxygen atom or a sulfur atom; R 1 represents a halogen atom or a lower alkyl group; R represents a hydrogen atom or a methyl group; R represents a halogen atom, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a lower alkylthio group, a cyano group or -COOR ⁴ (R ⁴ is a lower alkyl group, a lower alkoxyalkyl group or a group tetrahydrofurfuryl); m is 0, 1 or 2 and n is 0, 1,2 or 3 which comprises the step of reacting a compound represented by the following formula: 70 370 File: OP 89257 O with a compound represented by the following general formula: R - Y in which R has the same meanings as previously defined - 5 and Y represents a halogen atom or -O-SO - R (in which 5 ² R represents an alkyl group or an aryl group). Process according to claim 1, characterized in that the compound prepared is 2- [4-chloro-2-fluoro-5- {2- (4-fluorophenoxy) ethoxy} phenyl] -5,6,7,8 -tetrahydro-imidazo- [1,5a] -pyridine-1,3 (2H, 8aH) -dione. Process according to claim 1, characterized in that the compound prepared is 2- [4-chloro-2-fluoro-5- {2- (3-methylphenoxy) ethoxy} phenyl] -5,6,7, 8-tetrahydro-imidazo- [1,5a] -pyridine-1,3 (2H, 8aH) -dione. Process according to claim 1, characterized in that the compound prepared is 2- [4-chloro-2-fluoro-5- {2- (3,4-dimethylphenoxy) ethoxy} phenyl] -5,6,7 , 8-tetrahydro-imidazo- [1,5a] -pyridine-1,3 (2H, 8aH) -dione. Process according to claim 1, characterized in that the compound prepared is 2- [4-chloro-2-fluoro-5- {2- (2,4-dimethylphenoxy) ethoxy} phenyl] -5,6,7 , 8-tetrahydro-imidazo- [1,5a] -pyridine-1,3 (2H, 8aH) -dione. Process according to claim 1, characterized in that the compound prepared is 2- [4-chloro-2-fluoro-5- {2- (4-methylphenoxy) -1-methylethoxy} phenyl] -5,6, 7,8-tetrahydro-imidazo- [1,5a] -pyridine-1,3 (2H, 8aH) -dione. 7 - Process of preparation of a herbicidal composition characterized by comprising the association of a heterocyclic compound 70 370 File: OP 89257 -26represented by the following general formula O O d) in which R represents a group represented by the following formulas: or -chch ₂ o (oi position or (3) position; X represents an oxygen atom or a sulfur atom; R ^ represents a halogen atom or a lower alkyl group, R ^ represents a hydrogen atom or a methyl group; R represents a halogen atom, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a lower alkylthio group, a cyano or -COOR group (R and a lower alkyl group, a lower alkoxyalkyl group or a tetra group -hydrofurfuryl); m and 0, 1 or 2 and n and 0, 1, 2 or 3 as an effective component, in an amount effective as a herbicide, with an appropriate vehicle. Process according to claim 7, characterized in that the compound is 2- [4-chloro-2-fluoro-5-j2- (4-fluorophenoxy) ethoxy} phenyl] -5,6,7,8-tetra -hydro-imidazo- [1,5a] -pyridine-1,3 (2H, 8aH) -dione. 9 - Process according to claim 7, characterized 70 370 File: OP 89257 -27 because the compound is 2- [4-chloro-2-fluoro-5-} 2- (3-methylphenoxy) ethoxy} phenyl] -5,6,7,8-tetrahydro-imidazo- [1,5a ] -pyridine-1,3 (2H, 8aH) -dione. Process according to claim 7, characterized in that the compound is 2- [4-chloro-2-fluoro-5- {2- (3,4-dimethylphenoxy) ethoxy} phenyl] -5,6,7, 8-tetrahydro-imidazo- [1,5a] -pyridine-1,3 (2H, 8aH) -dione. Process according to claim 7, characterized in that the compound is 2- [4-chloro-2-fluoro-5- {2- (2,4-dimethylphenoxy) ethoxy} phenyl] -5,6,7, 8-tetrahydro-imidazo- [1,5a] -pyridine-1,3 (2H, 8aH) -dione. Process according to claim 7, characterized in that the compound is 2- [4-chloro-2-fluoro-5- {2- (4-methylphenoxy) -1-methylethoxy} phenyl] -5,6,7 , 8-tetrahydro-imidazo- [1,5a] -pyridine-1,3 (2H, 8aH) -dione.